Empire Files: Privacy, Control & the Darknet

August 4, 2017

Out of the periphery of most online users, there's a vast, hidden space used by people who want to remain anonymous, which filmmaker Alex Winter explores in his documentary Deep Web. The film focuses on the Silk Road, a black market hosted on the Darknet using bitcoin cryptocurrency, and the trial of Ross Ulbricht, who was given a double life sentence without the possibility of parole for creating and hosting the site.

Out of the periphery of most online users, there's a vast, hidden space used by people who want to remain anonymous, which filmmaker Alex Winter explores in his documentary Deep Web. The film focuses on the Silk Road, a black market hosted on the Darknet using bitcoin cryptocurrency, and the trial of Ross Ulbricht, who was given a double life sentence without the possibility of parole for creating and hosting the site.

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Story Transcript

Speaker 1: It’s hard to imagine life without the internet. But for a technology so pervasive in our lives, we know surprisingly little about how it works, or more importantly how to protect ourselves in the digital space, in the age of mass surveillance and data mining. Out of the periphery or most online users, there’s a vast hidden space in the ether used by hacktivists, drug dealers and anyone else who wants to remain anonymous. It’s called the Dark Web, a sub-sect of which filmmaker Alex Winter explores in his new documentary, Deep Web.

The film focuses on the philosophy and trial of the Silk Road, a black market using bitcoin crypto-currency hosted on the Dark Net. Adopted from the famous drug route across Asia, the Silk Road was created by young computer prodigy Ross Ulbricht, who called himself Dread Pirate Roberts. Ross started the Darknet project with the intention to radically confront the power establishment by circumventing the drug war, but ended up being made a public example of. Given a double life sentence without the possibility of parole.

With such an unprecedented punishment, obviously there was more to the story. Alex Winter, also an actor and privacy advocate attended Ross Ulbricht’s trial. Winter’s a longtime internet activist who has documented government persecution of web pioneers in multiple films included Downloaded about Napster, Relatively Free about Barrett Brown and now Deep Web, exploring the many precedents set by the Silk Road case.

I sat down with Alex Winter to discuss more about the Deep Web, the Silk Road and why encryption on things like signal still matter in light of the Wikileaks vault seven release.

So your film Deep Web obviously covers so much ground in telling the story of Silk Road. It was also narrated by Keanu Reeves, which was really cool. Your counterpart in Bill and Ted’s Excellent Adventure.

Alex Winter: Yeah.

Speaker 1: Let’s start with the basics, because this is a really hard topic for someone to delve into who doesn’t know anything about the Deep Web. What is the Deep Web? What’s on it? How big is it?

Alex Winter: Okay, that’s a really good question, because there’s a lot of misinformation around it like there is around anything involving cryptography and people who want privacy and anonymity in the digital space. So the Deep Web only refers to essentially technical gack. It’s just what’s under the hood of the internet. It’s un-indexed content. So it’s stuff that people aren’t interested in indexing, which mostly means banking data, the flotsam that flies around the internet that needs to exist there, but does not need to be indexed for any reason, code, that type of thing. And that’s gigantic. It’s just noise.

What happened was, there was an area called the Darknet. The Deep Web is very, very big, right? There’s an area called the Darknet that’s very, very small. And that’s where people actually commune. And so what cryptographers did over the years, is they drilled their way into this little space and they created tools like a browser called Tor, which has its own hidden service within the Darknet. And you can use Tor, that’s where the Silk Road black market showed up. And you can use it to communicate with other people. And it has an onion suffix instead of a .com suffix. And that’s essentially hidden away from public viewing.

That was initially created, even Tor itself was funded initially by the US government, the navy. But it was initially created mostly for intelligence communication that they wanted to be encrypted. But the way encryption works, if you’re the only one on the wire, then everyone knows you’re on the wire. Right? So the intelligence community didn’t want to be the only ones in the Darknet, the only people talking. If two guys with a styrofoam cup and a string, and there’s no one else there, they’re like, “Oh, that’s where the two guys from the NSA are, because there’s no one else there.”

They let that technology go out into the public. They wanted to populate that space, because then they can live amongst the noise. So it’s the simplest way I can put it. It’s a little complicated. But Deep Web is big and vast and meaningless for the average person. Darknet is teeny weeny and has things going on in it like intelligence people, people who just want to have privacy online. And people selling drugs and contraband and things like the Silk Road.

Speaker 1: Dissidents, journalists use it for these reasons too, so it’s not this nefarious criminal enterprise.

Alex Winter: Oh, not at all.

Speaker 1: A lot of good things happening-

Alex Winter: Not only is it not just nefarious, but it’s like looking at Manhattan and saying that Manhattan is a haven for drugs because there’s an alleyway where someone’s selling drugs. The large percentile of what’s going on on the Darknet isn’t crime related. It’s journalism, intelligence community communications. It doesn’t get publicized, because those people want privacy. So there was a very loud, and still to some degree is, noisy bias against the Darknet saying, “Oh, it’s all bad. It’s all drugs. It’s all guns.” But it ignores the fact that the people that are not doing those things don’t want to advertise. So they’re not making noise about being there.

Speaker 1: What was different about Silk Road when it first came into fruition, because it certainly wasn’t the first online marketplace for drugs and et cetera.

Alex Winter: No. I mean the internet has been driven by porn and drugs since there was an internet. And so there were drugs online at the very beginning of the internet, pre-web. The Silk Road was watershed. This was why I wanted to make a movie about it, because as far as the public or the DOJ or the government waking up to it was concerned, it was watershed because when it was created, it was combining Tor, which was this way to get into Tor hidden services with bitcoin, which was viewed as anonymous form of currency. By combining those two things, it attracted an enormous user base. So people started using it like crazy. And that’s why it scaled in a technical terms. That’s why it caught the eye of the DEA and places like that. And it also started to get press.

I think Adrian Chen in Gawker did a big article on it. It grew because it got press. And people started saying, “Oh, there’s this crazy community where people are exchanging drugs and all kinds of stuff.” So that made the government take notice. There are many reasons why the government took notice that are not obvious, which is what I wanted to get into in my film. And there are also many things about the Silk Road that are not obvious, which is what I wanted to get into in the film. So, to the public, the Silk Road was watershed, because, oh my god. You could buy heroin online, which you always could, but now it’s much easier, click of a button, whatever. To me what was watershed about the Silk Road was it was the first time in history that you had a large scale anonymous online community. And that matters. And that changed a lot permanently.

I had made a movie before Deep Web called downloaded about Napster. And my perspective on Napster was similar, which was that Napster was the first time in history that you had the first large scale online community period. It was the first time that you had 50-100 million simultaneous users moving through one central database, which again, it changed the world.

So I was very interested in the Silk Road when I learned about it, because when I got on the Silk Road before it got shut down. I didn’t care about drugs. I was there seeing that there were tens of thousands of people with anonymous user names in an anonymous community communicating about politics, philosophy, literature, drugs, whatever. There had never been anything really quite like that before and an anonymous environment. And that was, to me very striking.

Speaker 1: Your movie really, really does depict that other side of it that you obviously don’t hear in the press. It’s painted as this crazy, criminal conspiracy with Ross was a murderous scumbag who deserves to be locked away for life. But really your movie paints it as this beautiful organic thing that, especially in today’s day and age, good god. I mean nothing’s anonymous. So I could see the attraction of course. I wanted to talk more about these founding principles that Dread Pirate Roberts had and the site had, because I really do think that is the underpinning threat to the empire.

Alex Winter: Yeah, it’s threatening on a number of levels. The thing for me is that I first got interested in the internet in the late ’80s. And I got interested because A, I knew my way around technology. And I found this community there. And the community was very fascinating. It was what was called the BBS era, so you had all these different, all newsgroups. And you had what was called the alt section, which was like alt rec book, alt rec philosophy, alt rec art, alt rec drugs, alt rec sex. Everything you could possibly imagine, everyone was using anonymous user names and communicating and sharing data and media and all kinds of stuff. It was an amazing community. It was small. It was tens of thousands of people, but it was not millions of people.

And I found that really striking then. And it seemed like the beginning of something. There was a movement. For me, Napster was this huge boulder in the water, because now it was like, “Okay, now this is the democratization of culture. And what I noticed about Napster, which is why I sought out Shawn Fanning and wanted to make a movie about him then, which I did. I actually sought him out in 2000. The pushback against Napster was mythologized and I could tell that then, because I was a Napster user. So every time someone went on TV and said, Napster bad, you’re just pirates. Whatever. And I was thinking, “Well, I’m not a pirate. And most people that I know on Napster aren’t pirates. That doesn’t mean there aren’t pirates there.” Right? But the majority of the people I knew in the community were not there to pirate.

I started scratching my head going, “What is this pushback about?” And then you started investigating the RIA, the Record Industry Association and their relationships in DC and the threat. And it’s a funny thing, because like you said about the Silk Road. Yes, you have drugs, and you have bitcoin. You have all this stuff. And libertarians and anarchists and they’re openly talking about dismantling the system. That’s an obvious threat, but Napster was a huge threat to the power structure. And you weren’t getting that kind of blatant discourse. But they were terrified of it. And they were going to exterminate these guys to the fullest extent that they could and brand them in the public as evil, pirate people, an image I think they still have not really been able to shake.

When I saw the Silk Road, I realized it was the same thing, that whatever Ross’ motives were, and this is not to exonerate him. But whatever his motives were, clearly in his political views, in his own personal history, he was looking to create a massive safe haven online anonymous community where all of these ideas could be discussed. Whether people’s motives got corrupted, whatever, the reality of it is is the Silk Road was, at it’s heart a community mostly of pretty radical political thinkers and not of one stripe. Ross has libertarian leanings. Other people had hard core anarchist leanings. It was a genuinely democratized community. And it was an amazing place to wade around in. The conversations, these were really bright people.

Speaker 1: Yeah.

Alex Winter: And then you just had people there that would just buy weed or whatever. I mean that existed too obviously.

Speaker 1: No, I mean it’s incredible because like the documentary mentions, even though you had all these people, different radical political bents, everyone galvanized around the idea that the drug war is horribly detrimental to the society and that drugs should be obviously decriminalized at the very least.

Alex Winter: In the Silk Road case, the Silk Road was immediately built up as this much bigger thing, right? It immediately struck me that something was rotten in Denmark when it was like, billions of dollars in sales. Well that’s not true. This amount of users. That’s totally not true. I mean it had made an impact, but it was, in the scheme of things, a little weeny website and this very tiny section of the internet that nobody goes to and most people couldn’t figure out how to use even if they wanted to go there. And all the numbers were getting super inflated. But then you look at the drug war and you look at the existential existence of the DEA and the FBI and the amount of money, the prison system. And you’re dealing with a massive amount of power that is threatened by, not just the idea of what the Silk Road represents, which is the democratization, as you said, of people who want to talk against the drug war.

But what’s worse, I think what was scarier for them, which is what happened with Napster, was they saw the future. Obviously, the internet is going to be where drugs were sold. Obviously, the drug war is all about criminalization and not about medical help and treatment. Obviously, these people’s budgets are funded on the basis of this continuing and they would lose their funding if it stopped continuing. So the threat level was on so many different levels. Then you get Ross, moved from San Francisco to the southern district of New York. And when that happened, we all knew he was screwed, because then you add on to that the financial regulation concerns around bitcoin, which is all centered around the southern district, that’s Wall Street. That’s their beat.

So Ross just found himself jammed in the middle of surveillance operatives. He was breaking the cryptography rules and bitcoin, people were terrified on Wall Street about where bitcoin was going, especially in those days, they thought it was going to upend Wall Street, which is absurd. But they were going after him, you had the drug war people. They are going after him. And so it was just a perfect storm.

Speaker 1: The media floated around murder for hire theories that convicted Ross in the court of public opinion before the trial even happened. Yet, as Alex notes, he was never charged for them. Thoroughly demonized in the public, he was swiftly convicted of every crime committed by everyone on the site. The judge handed down a double life sentence without the possibility of parole. The FBI sting agents themselves were using the Silk Road to steal money during the operation. Shawn Bridges stole $800,000 in bitcoin, while informant Carl Forest siphoned $50,000. They also broke the law by hacking Ross’ computer without a warrant and using that evidence to arrest him.

Alex Winter: The idea that they just gave him that sentence because they were thinking of the children, which is how it was presented, the children, the children, is absurd. The Silk Road was a honey pot almost from the beginning. The feds were all up inside it. An enormous amount of the hard drugs that were being sold were being sold by federal law enforcement, both corrupt and straight up law enforcement. So a lot of the deaths that they were attributing to Ross were really directly attributable to different people of law enforcement agencies. So the hypocrisy was just staggering.

And for me, what was cut and dried was very simple which was, and this is the way I looked at it for the film, even if Ross was guilty of every single thing they claimed he had done, including the murders for hire scam. None of those charges merit a double life sentence without the possibility of parole. They just don’t. So it was somewhat of what I watched happen with Napster. It was a successful spin job in the sense that enough stuff got waved around and the children and all of that stuff that they always pull out, that the general public sentiment was like, “Screw them.” Basically, just whatever. And to me, that was a very strong indication of the politics of the case, of what they had at stake, what they felt an example they needed to make of him, how threatened they are by cryptography and anonymity and privacy and bitcoin and whatever. The over severity of the sentence to me was a tipping of their hand.

Honestly, when I went to the sentencing, even though I wouldn’t have agreed with it, had they given him 8-10 years based on drug kingpin charges, which is what the heaviest charge was, which was …Silk Road didn’t have drug kingpins. It was tiny. But it’s a little hard to argue with that given the potentiality of what the crimes were even though I may not have agreed with it.

But the double life sentence was just a tipping of the hand. It was so absurd and so completely unfair, that it makes you have to ask why they felt the need to hang him in that way.

Speaker 1: And also circumvent the law several times doing so.

Alex Winter: Completely.

Speaker 1: Amazingly, like you said, there’s other Silk Roads resurrected. You can’t kill the idea.

Aaron Swartz is another computer genius who posed a serious threat to corporate and government control. As a passionate activist for net freedom, Swartz believed that information should be free, especially when it’s paid for by the taxpayer. His so called crime was simply downloading academic journals out of reach to most people who don’t pay hundreds of dollars in fees to universities they fund with their taxes. The empire tried to crush him for it. He faced $1 million dollars in fines and up to 35 years in prison, essentially a life sentence. Exasperated and depressed, Aaron took his own life. According to Swartz’s dad, Aaron was killed by the US government.

Let’s move on to Aaron Swartz, because this is another prodigy who helped create open source technology. I wanted you to comment on that, because this is another person that the hammer came down so hard. Of course, we know what happened to him, the tragic suicide. Why was he such a threat? Why is open source technology such a threat?

Alex Winter: The words open source are terrifying to controlling interests whether it’s business or government. And there are some bad actors in those communities that will do anything to maintain control in a world where it’s very difficult to maintain control. There’s always this need to try to hang a label on something and then hammer it into the ground publicly. And Swartz, that’s what happened to him was he was not just an open source guy. He was one of the heads of a big activism organizations. He was a very charismatic leader. He was very well spoken. He was very articulate. He was very effective. He was a trifecta of threat. He was technologically adept. He was aggressively effective in his activism. And he was forward thinking in terms of politics and the machinery of, he was big into campaign fraud and voter/election fraud and the corruption. And what became the post-citizens united world.

So he would have been on many lists for those reasons. Then eventually, you’re looking at these lists going, “Wow, he’s on this list, and he’s on this list.” So he’s like, this is a bad person. This is someone that is a threat to us. It would be helpful for us to, if not put him in jail for a little bit of time, at least scare the shit out of him by coming at him with an enormous charge of prison time. And that’s a very common DOJ tactic.

Speaker 1: The Wikileaks recent Vault 7 release. I’m sure that you have been following it closely. The CIA has its own NSA style apparatus, totally unaccountable to everyone that it can do direct hacking into peoples devices, turn on microphones and turn into listening devices. What do you think this means? And also what will it do to the cryptography movement?

Alex Winter: If you’re using signal for instance. If you’re not a CIA target or whatever government target, because it’s obviously not just the US. That intelligence community have not hacked your phone. And it takes a lot to be a target on that level. Bt if they’ve hacked your phone, the way encryption works, if they own your box, as they say, it doesn’t matter what technology you’re using, because they’re sucking down your data before you encrypt it. And they’re reading the stuff that you get after you encrypt it, because they’re sitting on your shoulder watching what you’re doing through your technology.

That’s different than encryption. Encryption, if you’re not owned, which is a far greater of population of people who want to remain anonymous, journalists, dissidents, whoever, my kids for instance. I try to tell them to use this stuff. And you’re not owned, then that encryption is absolutely working and there is no evidence today that that has been broken. There is no evidence that suggests that they can read my signal communications or even some of my iMessage communications if they don’t own the box itself, either my phone or my laptop.

However, that being said, Snowden warned about this years ago now. I think many of us who deal with encryption or who are dealing sometimes with sensitive material have always taken it at face value that if somebody really wanted to get our material, they could. It’s negligent to assume, whether US state, actors or other intelligence operatives from other countries. I think it’s naïve to assume that if you are really a hard target that they’re not going to be getting into your system somehow. And you look at like what happened to Podesta whether you’re a tinfoil hat wearer or not, there’s a basic phishing scam. Operational security is really hard. And there’s no easy fix for it. There’s no app that just suddenly makes you secure. It’s a mindset.

Speaker 1: Well, it’s a fascinating schism right now. And it’s kind of like, where do we go from here, because you have the government that created these technologies. Of course, they’ve gotten so out of control out of their hands. And they don’t understand them anymore, like you said. It’s basically like hackers are on the forefront and on the edge of the technology and one step ahead of the government, whether it be Snowden or Barrett Brown or Aaron Swartz. Where do you see it going from here especially in light of the Russia hacking hysteria? Because on one hand, you can have just a claim based on nothing and we don’t have to prove it because it’s all in the ether. On the other hand, it’s almost like the faith of the world is put into the hacking community to try to save us from ourselves.

Alex Winter: Thankfully, the large percentage of the hacking community functions from a basic, there’s a reason you drive down the highway and people aren’t just constantly shooting each other and smashing into each other and driving into the median. We have to take it at face value that the large part of people who are brilliant enough to be very, very good at hacking have some form of moral compass. And if they don’t, that they’re going to get outmatched by those that do. Cryptography keeps getting better. I think that the Snowden revelations were such an important and necessary thing for the public to start to wrap its head around, because it’s not, as you said earlier, it’s exactly right. If you don’t allow people to go dark, if you penetrate the citizens’ ability to protect themselves, you are making them vulnerable and yourself vulnerable to bad actors. You are weakening the security of the internet. So it was vitally important that the average person has some understanding that they’re being surveilled and that they need some form of privacy.

There’s no doubt, we’re going to have to move into the world that includes the ability to go dark. That’s very scary to law enforcement. I understand why. If I’m in law enforcement, yes. I want to be able to open anyone’s door. And I don’t want anyone to have blinds on their windows, because they could be committing a crime. My job’s a lot easier if I can watch them do everything.

Unfortunately, it falls on the average citizen to know a little bit more about how their technology works than they may want to. Or a little bit more about what this stuff means. I think that for me, it’s a philosophical mindset. I think that if your government or your corporation or your mom or your kid or whoever is telling you that privacy is unnecessary and encryption is for people who are criminals are doing you a disservice. I think it’s more, really a shift of mindset. I think it’s understanding that you must have privacy in the digital space just like you demand it in the physical space. And I would say moreso.

I would say, we’re not all Emma Watson or people who literally have all their naked pictures hacked. It’s funny, but the reality of it is, is it’s just as easy to get your stuff as it is to get their stuff. And you don’t know whose hands that stuff’s going to end up in. You don’t know who’s going to end up with pictures of your kids. You don’t know what they’re going to do with those pictures of your kids. There are very bad people out there. Your banking information, your entire medical history. We just got this, I think most of us can agree, a fairly wonky political administration at the moment, right? A few years ago, people were like, “Well, why do I care about my government?” And now a lot of those people are going, “Oh, holy … I don’t want this administration coming after me because they have anti-Islamic tendencies or whatever crazy prejudices they have. Now suddenly, I’m a target.” It’s like all the people who voted for Trump now whose husbands and wives are being deported. We didn’t think we were the ones that were going to get … Right?

Speaker 1: Right. That’s the bad guys.

Alex Winter: Yeah. Exactly. The digital space is the same where you can suddenly, if your information is all freely there, you don’t know what someone is going to do with it. And what administration is going to do with it. So people, it’s a mindset, have to think a bit more prudently about how they protect themselves online.

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